Some common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 16681-65-5
A solution of n-BuLi (2.5 M in hexanes, 1.5 mL, 3.75 mmol) was added dropwise by syringe to a solution of 1-methyl-1H-1,2,3-triazole (324 mg, 3.90 mmol) in dry THF (20 mL) in a dry ice-methanol bath. The suspension was stirred for 30 minutes, slowly allowing the reaction mixture to warm to -20 C. (4-Chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (0.800 g, 1.89 mmol, Intermediate 46: step b) in dry THF (10 mL) was added to the mixture via syringe and the resulting mixture was allowed to warm to ambient temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride. Water was added and the aqueous mixture was extracted with dichloromethane. The combined organic layers were dried (Na2SO4), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography (silica gel, 0-5% MeOH-DCM) to provide the title compound. 1H NMR (400 MHz, CDCl3) delta 8.24 (d, J=1.9 Hz, 1H), 8.05 (s, 1H), 7.71 (d, J=8.7 Hz, 1H), 7.37 (dd, J=8.7, 2.0 Hz, 1H), 7.26-7.21 (m, 2H), 7.02 (s, 1H), 6.97-6.90 (m, 2H), 5.95 (s, 1H), 4.16 (s, 2H), 4.07 (s, 3H), 3.87 (s, 3H), 3.31 (s, 3H), 2.09 (s, 3H); MS m/e 506.9 [M+H]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16681-65-5, its application will become more common.
Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics